Kinetic Resolution of Aldehydes Bearing an All-Carbon Quaternary Stereocenter at the α-Position by the Antilla Allylboration DOI Open Access
Yuliang Chen, Fengkai He, Siyun Wang

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(12), P. 4294 - 4294

Published: Jan. 1, 2023

Acyclic aldehydes containing a chiral all-carbon quaternary center at the α-position are important synthons for pharmaceuticals and natural products.The challenges such as steric congestion conformational flexibility in acyclic systems must be overcome, which constitutes to hot difficult topic field of asymmetric catalysis.Such type structural motif is mainly accessed from α-C-H functionalization tertiary via enamine catalysis or based on enolate chemistry.Desymmetric tandem strategies have also been applied synthetic task.The discovery novel methods still highly demanding, especially an organocatalysis manner.Binaphthol (BINOL)-derived phosphoric acids demonstrated efficient bifunctional catalysts wide range organic reactions including allylboration (Antilla allylboration).We envisaged that if racemic α-all-carbon were applied, kinetic resolution through Antilla would provide homoallylic alcohols center.The idea was eventually realized by employing 10 mol% (R)-3,3'-bis-(2,4,6-triisopropylphenyl)-1,1'-binaphthyl-2,2'-diylhydrogenphosphate (TRIP) toluene -70 ℃. 15 examples bearing electron-rich, electron-neutral electron-deficient substituents phenyl ring, well 2-naphthyl group screened, affording moderate performance (with s-factor up 37.0).The ee values products reached 97% 81%, respectively.This method provides new route synthesis molecules stereocenter.

Language: Английский

Bipyridine-N,N′-dioxides Catalysts: Design, Synthesis, and Application in Asymmetric Synthesis of 1H-Pyrazolo[3,4-b]pyridine Analogues DOI

Shijie Zhu,

Xue Tian, Jichang Liu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(17), P. 3487 - 3492

Published: April 18, 2024

A novel type of highly efficient chiral C2-symmetric bipyridine-N,N′-dioxides ligand application in catalyzing Michael addition/Cyclization 5-aminopyrazoles with α,β-unsaturated 2-acyl imidazoles has been developed, affording the corresponding adducts 85–97% yield up to 99% enantioselectivity under mild conditions a lower catalyst loading and broad scope. Remarkably, this protocol exhibits advantages terms reactivity enantioselectivity, giving fact that as low 2.2 mol % L1 2.0 Ni(OTf)2 can promote title reaction on gram scale afford desired product excellent enantioselectivity.

Language: Английский

Citations

7
The Effect of Basic Ligands and Alkenes on the Regioselectivity of C−H Additions of Tertiary Amines to Alkenes DOI
Da Li, Yuji Wang, Shiyu Wang

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(32)

Published: April 4, 2024

Abstract Highly regioselective C−H alkylation reactions of tertiary anilines and alkyl amines with simple alkenes have been achieved by the use imidazolin‐2‐iminato scandium complexes. This protocol provided an efficient atom‐economical route to structurally diverse amine derivatives. The basic ligand, a coordinating THF in catalyst substitution alkene substrates were found switch regioselectivity presumably due generation different types catalytically active species or formation relatively stable intermediates. On basis deuterium labeling experiments KIE experiments, possible catalytical cycles understand reaction mechanism as well regioselectivity.

Language: Английский

Citations

5
Regioselective and asymmetric allylic alkylation of vinyl epoxides for the construction of allylic alcohols via synergistic catalysis DOI
Min Chen,

Longqing Yang,

Yuzhen Li

et al.

Science China Chemistry, Journal Year: 2023, Volume and Issue: 67(2), P. 542 - 550

Published: Nov. 17, 2023

Language: Английский

Citations

11
Facile Synthesis of Quinoline-Substituted 3-Hydroxy-2-oxindoles and 3-Amino-2-oxindoles via a Palladium-Catalyzed Cascade Intramolecular Cyclization/Intermolecular Nucleophilic Addition Reaction DOI

Huawei Lin,

Xinyan Hu, Bing Han

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 3413 - 3418

Published: Feb. 20, 2024

An efficient cascade intramolecular cyclization/intermolecular nucleophilic addition reaction of allenyl benzoxazinone with isatin or isatin-derived ketimine has been established by using Pd0-π-Lewis base catalysis. A series 3-hydroxy-2-oxindoles and 3-amino-2-oxindoles quaternary carbon atoms at the C3 position were synthesized in good yields under mild conditions through this protocol.

Language: Английский

Citations

4
BF3·OEt2 Catalyzed Cascade [4 + 2] Benzannulation of Vinyloxiranes with Coumarins to Construct Benzocoumarin Derivatives DOI
Yafei Wang, Yujia Wang,

Jiaxin Qu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(13), P. 9462 - 9472

Published: June 13, 2024

A BF

Language: Английский

Citations

4
Review on Catalytic Meinwald Rearrangement of Epoxides DOI Open Access
Yulong Zhang, Bowen Hu, Yushuang Chen

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(59)

Published: Aug. 14, 2024

The past few decades have witnessed tremendous development within epoxides. Among the many known reactions involving epoxide, Meinwald rearrangements represent one of most important and attractive approaches, which can transform epoxides into versatile carbonyl compounds. Given high efficiency this protocol, substantial efforts been made by researchers utilizing multiple catalyst systems. This review provides an overview recent advances in rearrangement (from 2014 onward), along with detailed discussions on mechanistic insights. aims to highlight importance value these methodologies, thereby promoting further investigation application.

Language: Английский

Citations

4
Regulating Steric Effect of Cobalt Corroles for Promoted Oxygen Electrocatalysis DOI
Yuhan Xu,

Xiaotong Jin,

Jieling Zhang

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 14350 - 14355

Published: Sept. 13, 2024

Language: Английский

Citations

4
Phosphine-Catalyzed Cascade Cycloaddition of Vinyl Oxiranes with Sulfonium Compounds to Step-Economically Construct Spiro-2(3H)-furanone Scaffolds DOI
Thomas P. Yang, Wei Du,

Chia‐Yu Wu

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 9, 2025

In this work, we developed a phosphine-catalyzed cascade lactonization/[2 + 1] annulation reaction between vinyl oxiranes and sulfonium compounds for the highly diastereoselective construction of spiro-2(3H)-furanone skeletons. The cycloaddition proceeds via 2(5H)-furanone phosphonium intermediate, introducing an oxygen-containing active intermediate phosphine catalysis. These findings highlight significant potential harnessing as versatile synthons constructing spirocyclic through simultaneous multicyclic skeleton formation.

Language: Английский

Citations

0
Transforming Carbohydrates Through Multicomponent Reactions: Advances and Applications DOI
Priyank Purohit, Ravi Kumar Mittal, Prabhat Kumar Upadhyay

et al.

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(15)

Published: April 1, 2025

Abstract This review highlights multicomponent reactions (MCRs) and their utilization in carbohydrate chemistry, where the anomeric center remains a concerning point maintaining selectivity is major challenge. Successful examples included involve synthesis of multifunctional carbohydrates with enhanced inherent physicochemical biological properties. compiles presents importance MCR which parent structure modified intact. explores various types MCRs applied to carbohydrates, highlighting synthesis, derivatization, functionalization molecules. The mechanistic aspects these highlight how unique structural features influence reaction pathways outcomes. applications fields glycomics glycoproteomics are shown, extension probability also discussed here. Through this comprehensive review, we provide insights into current state art identify promising future research directions that could further enhance utility impact chemical sciences. reader will be inspired perform for complex molecule expand use materials science.

Language: Английский

Citations

0
Catalytic Asymmetric [3 + 2] Cycloaddition of Exocyclic Enol Ethers for the Synthesis of Spiroketals DOI Creative Commons
Fengcai Zhang, Yuqiao Zhou,

Hansen Zhao

et al.

Precision Chemistry, Journal Year: 2023, Volume and Issue: 1(7), P. 423 - 428

Published: July 24, 2023

An efficient synthesis of chiral benzannulated spiroketals via catalytic asymmetric [3 + 2] cycloaddition exocyclic enol ethers with p-quinones was achieved. The transformation enabled by a N,N′-dioxides/TmIII complex as the Lewis acid catalyst and afforded series enantiomerically enriched spiroketal derivatives in good yields (up to 99%) enantioselectivities 98% ee). Topographic steric maps distribution buried volumes catalysts Cavallo's SambVca 2 tool were used elucidate enantioinduction raised ligands metal ions.

Language: Английский

Citations

9